Man Puzzled After Date Expects Him to Cover Her Babysitter Costs: “Is That Normal?”

Getting back into the dating world after years in a long-term relationship can feel like stepping into a whole new universe. The rules have shifted, dating apps reign supreme, and the charm that once worked a decade ago might now fall flat. It’s no wonder that re-entering the scene can be a bit overwhelming.

That’s exactly what one man experienced when he recently dipped his toes back into dating—and ended up with a situation he never saw coming. After planning a casual first date, he was caught off guard when his date asked him to cover the cost of the babysitter she’d hired for the evening.

Confused and unsure if this was a common expectation or totally out of line, he turned to Reddit for answers. Below is the full story, along with some strong opinions and helpful insights from fellow users who’ve seen it all.

This man wasn’t sure what would happen on his first date post-divorce

But he certainly wasn’t expecting the woman to ask him to pay for her babysitter

Man confused after date demands payment for babysitter, text on gray background.
Text message recounting a date with babysitter payment confusion.
Text conversation about a date at a Greek restaurant and bar; confusion over paying for a babysitter.
Text about a successful date, with a mention of walking her home and kissing goodbye.

Text exchange about date requesting money for babysitter, leaving guy confused about the situation.
Man looking confused while on a phone call, wrapped in a striped blanket, outdoors.

Text excerpt discussing a date where a man feels paying for a babysitter is excessive.
Text about understanding that kids are part of pursuing a relationship, related to confusion over a babysitter demand.

Man puzzled by date asking him to pay babysitter, no prior agreement noted.

Text on a white background discussing dating concerns and asking for advice.
Text about a man's date asking him to pay for her babysitter, leaving him confused.

Readers assured the father that her request was not normal, and many encouraged him not to schedule a second date

Comment discussing a date's babysitter request as incredibly tacky, with 7.2k points.

Comment on a social media post: "Asking for babysitting money on a first date is crazy.
Comment on a post about a guy confused by a date’s demand regarding a babysitter.
Reddit comment discussing confusion over paying for a date's babysitter, with advice against it.
Comment discusses confusion over date's babysitter demand.

Reddit comment reading "HUGE RED FLAG" about paying for a babysitter on a date.
Reddit comment on date refusing to pay for babysitter, calling it outrageous and ridiculous.
Reddit comment expressing confusion over date requesting babysitter payment.
Text post about a confused guy whose date demands he pay for her babysitter, calling it tacky.

Comment discusses a date's demand for babysitter payment, calling it inappropriate and advising against future dates.
User comment discussing date babysitter payment expectations.
Reddit comment mentions paying for a date's babysitter as "not normal," suggesting further demands.
User comment on paying for babysitter during a date, calling it a financial red flag.

Comment suggests babysitting date's kid to earn 100 euros, related to confusion over paying for babysitter.
Reddit comment about not paying for a babysitter on a date as it's not the guy's responsibility.

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